Hydroxyamine hydrochloride → HCID 136393701, compound

HRID 1788889Notes

Reaction equation

HRID 1788889 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[CH2:9]([O:11][C:12](=[O:26])[C:13](=O)[C:14]1[C:22]2[C:17](=[C:18]([CH2:23][CH3:24])[CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[CH3:10]>O.C(O)C>[CH2:9]([O:11][C:12](=[O:26])[C:13](=[N:7][OH:8])[C:14]1[C:22]2[C:17](=[C:18]([CH2:23][CH3:24])[CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[CH3:10]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 14010219Ethyl (7-ethyl-1H-indol-3-yl)(oxo)acetate

Product 1

HCID 136393701HCID 136393701, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Solutions of sodium acetate (43.7 g, 0.53 mol) in water (100 mL) and hydroxylamine hydrochloride (37 g, 0.53 mol) in water (100 mL) were added to 7-ethyl-α-oxo-1H-indole-3-acetic acid ethyl ester 4 (17.4 g, 0.07 mol), in ethanol (250 mL) and the mixture was heated at reflux for 12 hours. The ethanol was removed by distillation and the resultant precipitate was filtered and recrystalized from hot ethanol to give the product (13.8 g, 75%), m.p. 167°-169° C. as a mixture of isomers.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 12 hours
  3. customThe ethanol was removed by distillation
  4. filtrationthe resultant precipitate was filtered
  5. customrecrystalized from hot ethanol

Sources & evidence

ORD record
ord-589aecb4d1ef418abc0ff082e9f786cc
Source dataset
uspto-grants-1987_08
Patent number
US04686213

Reaction notes

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